Background: High rates of psychopathology were found amongst deaf adolescents, but little is known about the psychosocial risk factors. This study investigated whether (1) less severe deafness and/or acquired or otherwise complicated deafness, and (2) having mainly contacts with hearing people, each represent chronic stressful conditions that moderate the associations between self-esteem and emotional problems. In addition, the moderating effect of observed peer rejection on the association between social acceptance and behavioural problems was explored. Method: Deaf adolescents of normal intelligence (N = 68) completed the Self Perception Profile for Adolescents. Psychopathology was assessed using a semi-structured interview with adolescents and reports by parents, teachers and expert ratings. Data on moderator variables were collected from school records, parental and teachers' reports. Results: Emotional mental health problems were negatively associated with self-esteem and positively with peer rejection. The association between self-esteem and emotional problems was moderated by the deafness variable less severe deafness or acquired or otherwise complicated deafness. Behavioural mental health problems were positively associated with social acceptance and peer rejection but negatively with the amount of involvement with hearing people. Peer rejection moderated the association between social acceptance and behavioural problems. Conclusions: The findings emphasise the importance of considering self-concept dimensions, peer problems and deafness- and context-related characteristics when assessing and treating deaf adolescents.